When The Best Conference Speaker Is Your Uber Driver (Epsilon Connect 2023 Notes)

Matt Zeigler is a Managing Director and Private Wealth Advisor with Sunpointe Investments, and he’s been helping people with their money for more than 15 years. He’s also one heck of a writer and publishes an excellent daily (!) note on his Cultish Creative blog and newsletter, which you can subscribe to here. We hope to start publishing Matt’s work on a regular basis and figured there was no better place to start than with his notes on our Epsilon Connect 2023 conference!

You can contact Matt at [email protected] and on Twitter at @cultishcreative. As with all of our guest contributors, Matt’s post may not represent the views of Epsilon Theory or Second Foundation Partners, and should not be construed as advice to purchase or sell any security.

The best speaker at Epsilon Connect 2023 was my Uber driver.

The conference was filled with smart, curious, and successful people from all walks. Finance, politics, tech, medicine, music, small business, big business, (insert a “holy crap you did/do that?!” profession), and it was awesome to all be at Vanderbilt together.

But this Uber lady.

Maybe you don’t know how it gets in Nashville in the summer. 90-something degrees. Impending thunderstorm complete with sawed-off warning shot thunder. The official cocktail hour ended 30 minutes ago, the unofficial one is already underway, and the ride you politely declined 60 minutes ago ain’t coming back.

You find yourself hailing an Uber under an oak tree straight out of the Charlie Brown Christmas Tree Lot. It’s barely shielding the rain, and despite deserving to be mercy-struck by lightning, you’ve calculated it probably won’t because it’s short and the gods are as nice as the people around here. Or so you hope.

In its shelter, you call your significant other to assure them, “I’m still alive – at least for now!”

I’ll take this story back to being about me now. And my uber lady.

The lifted pickup truck pulls up (Nashville, I adore you), I hop in, she says, “Buckle up honey” at the same time my girlfriend Val is telling me, “Don’t forget to wear a seatbelt” over the phone. As the belt-buckle clicks and my eyes land on the bobble-head chihuahua on her dashboard, I feel both loved and safe.

My driver is early-retirement age, with short grey hair and an “I needed a few extra bucks and something to do after stepping down from being a middle school teacher” vibe. I ask the polite-yet-standard question, “So how long have you been driving for Uber? Do you like it?”

This Uber lady. My UBER lady. Best speaker at the conference. Here’s her opening:

“I’ve been driving for a few years now. Ever since I had to retire. I used to drive big rigs. It’s nice I get to drive still. But I sure do miss driving my big truck.”

Me, doing my best Grant Williams, “Aww, that’s so cool you knew what you loved and found a smaller way to still do it. Why’d you stop driving the big rigs?”

The truck made the turn onto a highway. Which is notable because of what she said next.

“I stopped driving after I had my accident. It was a bad one. Couldn’t drive anymore after that.”

Sweet Nashville gods, don’t fail me now.

“That’s awful, I’m so sorry to hear that.” I glanced at the GPS cradled on the dash. We had 20 minutes to go and were doing 60 in light rain. If I was going down, I might as well get her story first. “Were you hurt?”


I need to pause here and let you know what was going on at this conference. Ben HuntRusty Guinn, and friends (and family) are really onto something.

Epsilon Connect is basically a gathering for people who have figured out how to make models work for them. Not in a mercenary way, but in a “We all have found success without hurting others, so how do we now make others successful while reducing the success-via-hurting-others models that seem to be everywhere and making people like us sad/jaded/cynical when we don’t want to be” way.  

Or at least that’s why I’m there and hoping it’s why the others are there too.

I believe most people’s default mode is to care. I believe you don’t have to go to Church™ about it. I also believe you need people in your life who mutually care. What makes the Epsilon crowd so enticing is we all are trying to figure out how to help others care productively.

Not to escape reality. Not to be shielded from reality. To help reality be less annoying.


You think something is wrong with the world and you’re not wrong to think that. But you know you’re not right about it either. The expression “the map is not the terrain” is useful here.  We can model reality (or markets, or elections, or…) but there’s always a gap between the details on the map and the recently fallen branch on the sidewalk just outside your house.

The gaps represent the statistician’s favorite fudge factor. They’re the comedian’s room for exaggerations. They’re the musician’s laggiest kick drum or rushiest snare. The gaps define the model as much as they’re poetically used to explain the reality. We need the gaps. And we need to talk about the gaps. So badly that we gathered for a conference about them.

Epsilon is the technical term for the variable in an equation that closes the gap between the model and the reality.

Epsilon Theory is the idea we can’t talk about the models without also talking about the gaps between where the map’s resolution ends and the real world gets all nuanced.  All productivity AND all counter-productivity is tied to the gaps, to the epsilon, to the differences between the map and how we talk about the map.

Epsilon Connect is a conference for people who think about the gaps. How the gaps have benefited them. How the gaps can benefit others. How the gaps can be used to hurt others. How we can take models that help without hurting and try to spread this gospel of (lower-case, non-trademarked) love in all of our communities.

OK, now back to the Uber lady. I know you’re really here for her presentation.


A recklessly speeding driver hit her truck head on. The driver didn’t make it. She hurt her back. The legal settlement was minimized because she didn’t say the right settlement-maximizing words in her police report. The confidence gap of the dead driver, the interpretive gaps of the police report and legal system.

She’d seen death and misfortune before. With both of her parents, who she was cursed and blessed to be with when each of them passed. Not in the peaceful way we all want to go out either. But that’s life in the gaps – finite and beyond expectation.

Her husband is trans. The whole family – the kids, the grandkids, and the extended family accept her husband for who she is. Except my driver’s sister. It’s causing a rift. One that feels like the original pain that kept it all a secret 30 years ago. The gaps have their own dynamics, and they change as much across models as they do across realities.

I was getting seriously schooled on gaps in the backseat of a pick-em-up taxi. It was the whole conference in a 23-minute autobiography.

And I can’t skip this last part from the end of my ride

On the topic of her marriage, she told me, “Some people thinks it’s strange we stayed together. I know that. But nobody has ever loved me like she has. She always was and always will be my husband and what do I care if she wants to wear a dress?”

I may or may not have cried a little at this point.

The gaps. They’ll break your heart. Wide open. If only you’ll let them.

We pulled inside the fence at my destination. I thanked her for sharing, she thanked me “for listening to an old trucker babble.” She got a big tip. I got a bigger one. An uber-big one.

Epsilon Connect wasn’t just about the big ideas, cool people, and the amazing new research project they’re rolling out at Vanderbilt (FABLE!). Epsilon Connect was about what my buddy Scott said to me after we walked out of one of the sessions, 

It all comes back to how you can’t change THE world, but you can change YOUR world, and sometimes THEIR world. And however you’re changing it, if you do it over and over, it adds up. Everybody here gets reverse-engineering what’s adding up, where, and wants to ask why. This is so cool.

My uber lady got it too. We’re all in this together. With Clear Eyes, Full Hearts, and a Friday night bright dream to not lose.

We have a lot of work to do until next year’s conference. Buckle up honeys.

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  1. Avatar for drrms drrms says:

    Wow. I learned at least as much about what Epsilon Theory really is from your piece @MZeigler3 than I probably have from any other piece.

    All productivity AND all counter-productivity is tied to the gaps, to the epsilon, to the differences between the map and how we talk about the map.

    Nicely done. Thanks!

  2. that is some seriously high praise Richard, thank you (!)

    this is the goal - if my Uber driver already gets what everybody in the conference got, how do we get more people talking to each other about this stuff with clear eyes and full hearts?

  3. Avatar for Laura Laura says:

    I’m thinking about the meaning of productivity, i.e. a product, a multiplier. AND how this is very different from a zero sum game. How might we lure people away from playing zero sum games? I really believe the full heart piece must come first, that’s where we truly connect if you think about it in gesture.

    Thanks for writing and sharing this. I got a lump in my throat too.

  4. Good stuff, well done!

  5. thanks for reading Laura.

    For all the times we barely hear the flight attendant telling us to put our masks on first, they’re really onto something.

    It’s a great time to go (re)read @bhunt and @rguinn 's notes on the stag hunt. It’s all right there if we can help others see it too.

  6. Epsilon is the technical term for the variable in an equation that closes the gap between the model and the reality.

    Epsilon Theory is the idea we can’t talk about the models without also talking about the gaps between where the map’s resolution ends and the real world gets all nuanced. All productivity AND all counter-productivity is tied to the gaps, to the epsilon, to the differences between the map and how we talk about the map.

    Thank you Matt for simply articulating the essence of Epsilon Theory for me. This is why I’m here.

    Jim Handshaw

  7. This is a great note. My favorite line being

    …but there’s always a gap between the details on the map and the recently fallen branch on the sidewalk just outside your house.

    That’s how I feel about everything from modern portfolio theory to politics and science. But even here at ET, I sometimes forget that this is the “origin” of this place. In my own life I always find myself a defender of the “gray”/non-white/non-black. That is the only way I know how to be, but it is exhausting at times and I often long for the ability to settle down permanently on the black of white.

    ET makes me feel less alone and your note reminded me of that - so thank you.

    I also love your Charlie Brown inspired profile pic, Charlie Brown/Peanuts being my second-favorite comic of all time (after Calvin & Hobbes). My non-religious family, religiously watch “A Charlie Brown Christmas” every Christmas Eve. I think it might be my favorite Christmas ritual!


  8. Thanks Em. I think we’re all here because we see them, and need the reminder the gaps are where the hope lives too.

    ps. Charlie Brown Christmas = seasonal staple. Credit for the picture goes to deadlymike, this is his “Dilla Schroeder” (which I’ll probably write about in a future note)

    Special shoutout to the actual branch that was on our sidewalk, and the couple who walks by every night and politely moved it into the grass where nobody could trip on it. Because our sidewalk is also a place they walk.

  9. thanks Jim, and glad you’re here too. Keep noticing the gaps.

  10. Avatar for Pat_W Pat_W says:

    Great read! Great writing.

    I must add my echo of the Uber Lady. My spouse is transgender- picture a Black Church lady. And we are old folks. She ‘came out’ at retirement time in late 2015.

    When things have been really bad for me (I broke my neck in 2008 and became a quad) she was right by my side twice a day even though she was working 12 hours a day. In my mind she’s still my guy and it never much mattered to me how people dress. Why should I care now?

    Because of the damn lipstick smears!!!

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